Throughout the software development process, before and after the software reaches production, it is necessary to create documentation to communicate the use, administration, and interfaces of the software with the development team, stakeholders, and end users. Manual creation of software documentation is difficult, time consuming, and expensive. Automated software documentation systems typically execute test scripts to run software applications through particular operational scenarios. One exemplary automated documentation system produces natural language textual descriptions of graphical user interface (GUI) object activity during the script-based execution of the software; the textual descriptions then are combined with screenshots of the graphical user interface that are captured manually during playback of the script to produce documentation for the software. Another exemplary automated documentation system updates existing software documentation using test scripts that include tags at locations in the test script that trigger the capture of respective screenshots of the software GUI at particular times during the execution of the test script; the screenshots then are incorporated into the documentation at designated locations that correlate with the tags in the test script.